Caribbean Villa Rentals

Know Before You Go...

Miles of magnificent ocean views; secluded private islands; white sand beaches at your doorstep are closer than you think--a click or a phone call away, actually. Whether you want to experience it all, or take a minimalist approach, our island experts have you covered. Choose from luxury villas in Anguilla, Barbados, St. Barts, St. John, St. Lucia and other Caribbean destinations. Many Caribbean villa rentals provide maid service, personal chefs and concierge services!

The only thing better than being in a tropical paradise is pretending it's your home. Our Caribbean villa rentals do just that. Live in your own private beach house with the amenities of a hotel or resort. We represent luxury villas in Anguilla, St. Barts, Turks and Caicos, St. John, and many other Caribbean islands. Start browsing. You're sure to find your perfect Caribbean villa rental.

It's been a long year. You've earned an unbelievable vacation. Don't leave it to chance. Our extensive listings of Caribbean hotels and resorts, restaurants, maps, and photos give you a better understanding of Caribbean destinations like Barbados, St. Lucia, St. Thomas, St. Martin and more. With so many hotel options, you may need to make two trips!

What Travelers Say About WhereToStay.com...

"We're all big fans of your site and I'm particularly impressed with the customer service support." - Cheryl

"Thank you so much for guiding us through one of the most spectacular vacations of our lives. I could not have imagined a more beautiful trip."
- C. Stack

"Thank you for making our vacation to Turks and Caicos the fantastic experience it was. We would definitely recommend WhereTo Stay." - Rosalia

"Once again thank you for all your help in making it a memorable holiday." - Faisal

"Everything was lovely. We enjoyed our stay immensely and I would not hesitate to recommend your company to anyone." - Kelly S.

The Caribbean Villa and Hotel Experts

We'll prove it - give us a call!

Knowledge is power - especially with vacation planning. That's why our Know before you go...® philosophy is so vital. We share the prime times for Caribbean travel; offer real travel reviews on Caribbean villa rentals; reveal the best beaches in Anguilla, St. Lucia, Barbados and more. Little convincing is needed when considering a Caribbean vacation. You just want to make the best choice. Our more than 15 years of experience enables us to provide honest, unbiased opinions about Caribbean rentals, restaurants and tourist attractions.

Luxury Villa Rentals & Concierge Services

Our experience and customer service set us apart.

Why not let your vacation begin in the planning stage? Sit back, relax, and let WhereToStay.com's villa rental experts do the legwork for you. It's like having your own personal assistant (you'll have to get your own coffee, though). We'll help find your unique Caribbean getaway. In addition, we'll arrange car rental, meet and greet, grocery pre-stocking, chef services, childcare, spa services, excursions and much more. We leave no grain of sand unturned, so your vacation can begin... well... here!

We Know The Caribbean

Our Focus, Our Expertise

Founded in 1995, WhereToStay.com is the original Caribbean travel review site, providing aspiring vacationers with real travel reviews on Caribbean rentals, restaurants, entertainment and more. Today, WhereToStay.com represents hundreds of Caribbean villas, hotels, private islands and resorts. Our Caribbean villa rental experts have traveled to the islands, stayed in the villas and can help you make the best decision for your unique rental needs. We invite you to explore our site and review our luxury vacation rentals and Caribbean destinations.

WhereToStay.com Verified

The "Where To Stay Verified" stamp of approval is your assurance that what you see is what you get. Our team of Caribbean villa rental experts visit, inspect and personally select only those villas which have passed our high standards. We give our honest and unbiased opinions, after all, if we wouldn't stay there, why would you?

Why Rent a Villa?

Why rent a Caribbean villa instead of a hotel or a resort? In addition to providing great value, villas are your home away from home and where the kitchen is always open! Kick back and relax in your own personal living space or by your own private pool. Away from the hotel and cruise ship crowds, villas allow you to truly experience the heart of island life. Learn more...

Contact WhereToStay.com

Our Caribbean villa rental experts frequently travel to the Caribbean islands, stay in the villas and can help you decide where to eat, where to shop and most importantly where to stay! Our goal is to help you Know before you go...®!